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Our top choices for Chesapeake condo rentals

Indoor pool
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
2.5 star property
Chesapeake
8.0 out of 10, Very Good, (4)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
$144 nightly
The price is $165
Dec 31 - Jan 1, 2026
Total with taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Indoor pool
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
10.0 out of 10, Exceptional, (1)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
$134 nightly
The price is $154
Dec 30 - Dec 31
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Dining
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
$135 nightly
The price is $156
Dec 29 - Dec 30
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Dining
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
$144 nightly
The price is $165
Dec 31 - Jan 1, 2026
Total with taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Outdoor dining
Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.

Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.

Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.
Northeast Virginia Beach
10.0 out of 10, Exceptional, (39)
"Exactly how described, nice location, host is very responsive."
United States
Melissa B.
$353 nightly
The price is $408
Jan 5 - Jan 6, 2026
Total with taxes and fees
Awesome Beach Getaway! 1 block to the ocean, with a big pool in the back.
Beach nearby
New! 3Bd 2Bth Oceanfront / Pool / Boat /224b

New! 3Bd 2Bth Oceanfront / Pool / Boat /224b

New! 3Bd 2Bth Oceanfront / Pool / Boat /224b
Sandbridge
8.0 out of 10, Very Good, (1)
"This room is not oceanfront, there is no view of the ocean.In my experience oceanfront means full on view of the ocean, ocean view means side view. Obstructed view is just that. What we had was NO view of ocean. Even though it says that. Very nice condo otherwise.Finding your parking space is like looking for Waldo,kinda crazy.One suggestion is a towel or bath mat to step on when you get out of the shower. There are no extra towels for that."
United States
lori h.
$583 nightly
The price is $660
Dec 30 - Dec 31
Total with taxes and fees
New! 3Bd 2Bth Oceanfront / Pool / Boat /224b
Pool
NEW! Oceanfront Triton's Treasure 3 Bd / Pool/ Gym

NEW! Oceanfront Triton's Treasure 3 Bd / Pool/ Gym

NEW! Oceanfront Triton's Treasure 3 Bd / Pool/ Gym
2.0 star property
Sandbridge
9.0 out of 10, Wonderful, (6)
"Great place to stay! Super close to the beach and it wasn’t too crowded. Has basics for what you need. The second parking spot was a little further away than ideal but we made it work. "
United States
Danni R.
$571 nightly
The price is $646
Dec 30 - Dec 31
Total with taxes and fees
NEW! Oceanfront Triton's Treasure 3 Bd / Pool/ Gym
Fridge, microwave, oven, stovetop
Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach

Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach

Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach
2.0 star property
Northwest
10.0 out of 10, Exceptional, (4)
"Great location , with restaurant across the street Amy family and I enjoyed our stay "
United States
shantielle T.
$563 nightly
The price is $649
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy 3-bedroom condo with AC and WiFi in charming Virginia Beach
Terrace/patio
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views

❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views

❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
Sandbridge
9.2 out of 10, Wonderful, (35)
"Excellent host! "
United States
Cindy S.
$609 nightly
The price is $710
Dec 29 - Dec 30
Total with taxes and fees
❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
Beach nearby
Oceanfront Condo with Indoor Pool

Oceanfront Condo with Indoor Pool

Oceanfront Condo with Indoor Pool
Northeast Virginia Beach
8.0 out of 10, Very Good, (3)
"Our daughter and family enjoyed the pool and beach. Thanks for prompt responses when I had questions!"
United States
Jan F.
$412 nightly
The price is $471
Dec 29 - Dec 30
Total with taxes and fees
Oceanfront Condo with Indoor Pool
Beach nearby
New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym

New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym

New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym
Sandbridge
8.8 out of 10, Excellent, (5)
"We attended a wedding and this place was the perfect location just across the street from the venue. There was another car parked in our reserved spot that made it difficult to get the key fob and return it but other than that it was a great place to stay. "
United States
Tracy N.
$558 nightly
The price is $631
Dec 30 - Dec 31
Total with taxes and fees
New! Island Breeze/3Bd/Oceanfront/ Beach/Pool/Gym
Beach nearby
New! Beachfront 3bd / 2Bth/Pool/Hot tub 104A

New! Beachfront 3bd / 2Bth/Pool/Hot tub 104A

New! Beachfront 3bd / 2Bth/Pool/Hot tub 104A
Sandbridge
10.0 out of 10, Exceptional, (2)
"Great stay, wonderful location, and the place is bigger than it looks in the pictures. Would definitely stay again"
United States
John C.
$578 nightly
The price is $652
Jan 4 - Jan 5, 2026
Total with taxes and fees
New! Beachfront 3bd / 2Bth/Pool/Hot tub 104A
Beach nearby
High floor, Ocean View Condo

High floor, Ocean View Condo

High floor, Ocean View Condo
Northeast Virginia Beach
$216 nightly
The price is $250
Dec 29 - Dec 30
Total with taxes and fees
High floor, Ocean View Condo
Beach nearby
Beachfront Penthouse! 4Bd/3Bth

Beachfront Penthouse! 4Bd/3Bth

Beachfront Penthouse! 4Bd/3Bth
Sandbridge
9.4 out of 10, Exceptional, (23)
"Proximity to the ocean was great."
United States
Raymond J.
$852 nightly
The price is $968
Dec 29 - Dec 30
Total with taxes and fees
Beachfront Penthouse! 4Bd/3Bth
Smart TV
Mountain Jade Garden Condo Resort 2 bed 2 bath near Newport News City Center

Mountain Jade Garden Condo Resort 2 bed 2 bath near Newport News City Center

Mountain Jade Garden Condo Resort 2 bed 2 bath near Newport News City Center
3.0 star property
North Newport News
6.6 out of 10, (4)
"Everything was clean and beautiful "
United States
Antwaine J.
$337 nightly
The price is $389
Dec 29 - Dec 30
Total with taxes and fees
Mountain Jade Garden Condo Resort 2 bed 2 bath near Newport News City Center
On the beach, sun loungers
Virginia Beach, oceanfront, boardwalk, beach, fun, dolphins

Virginia Beach, oceanfront, boardwalk, beach, fun, dolphins

Virginia Beach, oceanfront, boardwalk, beach, fun, dolphins
Northeast Virginia Beach
8.8 out of 10, Excellent, (18)
"Good visit"
United States
Elizabeth E.
$634 nightly
The price is $731
Jan 6 - Jan 7, 2026
Total with taxes and fees
Virginia Beach, oceanfront, boardwalk, beach, fun, dolphins
Property grounds
Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks

Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks

Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks
Sandbridge
9.4 out of 10, Exceptional, (20)
"Great stay and great condo!"
United States
Kevin F.
$882 nightly
The price is $1,003
Jan 2 - Jan 3, 2026
Total with taxes and fees
Waterfront Penthouse! 4bd/4Bth, 3000 sqft, 2 Decks
On the beach, beach towels
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission

OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission

OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
Northeast Virginia Beach
8.0 out of 10, Very Good, (15)
"Loved the location and the avtivitoes/events in the neighborhood."
United States
Smain K.
$661 nightly
The price is $762
Dec 29 - Dec 30
Total with taxes and fees
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Hotel Reviews

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

10/10 Excellent
"Staff was very helpful and friendly throughout our stay. The floor and area of my room was peaceful and quiet. The room was very clean and comfortable."
Saundra 4-night trip
Posted 12 hours ago
Comfort Suites Chesapeake - Norfolk

Find out more about Chesapeake

Chesapeake Condo Rentals information

Number of reviews
164
Accommodation
484 Condo Rentals
Lowest Price
$154
Highest Price
$1,003

Frequently asked questions

Why book your condo in Chesapeake with Expedia?
Booking a condo in Chesapeake is as simple as clicking on your travel dates and choosing an option that suits your style. Looking for something upscale or budget friendly, or a stay that also features a pool and free WiFi? Use Expedia's search filters to further narrow your search results and find the perfect fit.
How can I find cheap condos in Chesapeake?
An excellent way to find cheap condos in Chesapeake is with Expedia's easy-to-use filter tool. Tailor your search results by star rating, budget and amenities to discover unbeatable deals in a few clicks.
What is there to do in Chesapeake near my condo?
Chesapeake has enough experiences to keep you occupied for weeks (or months!), beginning with Chesapeake Golf Club. Oak Grove Lake Park, Cahoon Plantation Golf Course and Chesapeake Square Mall are other awesome attractions. If you're lingering longer, Greenbrier Mall and Chesapeake Veterans' Memorial are worthwhile additions to your itinerary.

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